methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Base Information

Chemical Name:methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate
CAS No.:1263198-01-1
Molecular Formula:C₂₃H₂₉ClN₄O₆S
Molecular Weight:525.025
Hs Code.:

Synonyms:methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

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Chemical Property of methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

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Technology Process of methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

There total 15 articles about methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

: 1263197-96-1
methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

: 95-51-2
o-chloroaniline

: 1263198-01-1
methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: methyl (3S,5R)-5-[(1,1-dimethyl-2-oxoethyl)amino]-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate; o-chloroaniline; With acetic acid; In toluene; at 130 ℃; for 4h; Dean-Stark;

With sodium tris(acetoxy)borohydride; In toluene; at 20 ℃; for 16h; Dean-Stark;
DOI:10.1016/j.bmc.2013.06.057

Reference yield:

: 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester

: 1263198-01-1
methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: C₂₈H₂₇F₆N₃O₃S / tetrahydrofuran / 24 h / -20 °C

2: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4: triethylamine / dichloromethane / 1 h / 20 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 1 h / 20 °C

6: dichloromethane / 2 h / 20 °C

7: N-chloro-succinimide / dichloromethane / 2 h / 20 °C

8: 18 h / 60 °C

9: hydrogenchloride / dichloromethane; water / 4 h / 40 °C

10: thionyl chloride / 1 h / 20 °C

11: acetic acid / toluene / 2 h / 110 °C

12: sodium cyanoborohydride / 6 h / 20 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; C₂₈H₂₇F₆N₃O₃S; diphenylphosphoranyl azide; sodium cyanoborohydride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 2: |Curtius Rearrangement;
DOI:10.1016/j.bmcl.2012.09.103

Reference yield:

: 534572-20-8
(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

: 1263198-01-1
methyl (3S,5R)-5-{[2-(2-chloroanilino)-1,1-dimethylethyl]amino}-1-(2-nitrophenyl)sulfonylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: diphenylphosphoranyl azide; triethylamine / toluene / 15 h / 90 °C

2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3: triethylamine / dichloromethane / 1 h / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 1 h / 20 °C

5: dichloromethane / 2 h / 20 °C

6: N-chloro-succinimide / dichloromethane / 2 h / 20 °C

7: 18 h / 60 °C

8: hydrogenchloride / dichloromethane; water / 4 h / 40 °C

9: thionyl chloride / 1 h / 20 °C

10: acetic acid / toluene / 2 h / 110 °C

11: sodium cyanoborohydride / 6 h / 20 °C

With morpholine; hydrogenchloride; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; diphenylphosphoranyl azide; sodium cyanoborohydride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 1: |Curtius Rearrangement;
DOI:10.1016/j.bmcl.2012.09.103